Preparation of Phenolic Paclitaxel Metabolites
- 1 January 1996
- journal article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 39 (14) , 2705-2709
- https://doi.org/10.1021/jm960142x
Abstract
The synthesis and biological evaluation of the two known phenolic metabolites of paclitaxel are described. The C3‘-phenolic metabolite 2 of paclitaxel was prepared from 7-(triethylsilyl)baccatin III (8) and enantioenriched N-benzoyl-2-azetidinone 7. The C2-phenolic metabolite 3 was synthesized from paclitaxel (1a) via selective C2 debenzoylation and reacylation.Keywords
This publication has 11 references indexed in Scilit:
- Partial synthesis of major human metabolites of docetaxelTetrahedron, 1994
- Internal Nucleophile Assisted Selective Deesterification Studies on Baccatin III. Synthesis of 2-Debenzoyl- and 4-Deacetylbaccatin III AnalogsThe Journal of Organic Chemistry, 1994
- Structures of the major human metabolites of docetaxel (RP 56976 - Taxotere®)Tetrahedron Letters, 1994
- Unexpectedly Facile Hydrolysis of the 2-Benzoate Group of Taxol and Syntheses of Analogs with Increased ActivitiesJournal of the American Chemical Society, 1994
- Isolation, Structural Determination, and Biological Activity of 6.alpha.-Hydroxytaxol, the Principal Human Metabolite of TaxolJournal of Medicinal Chemistry, 1994
- Taxol metabolism in rat hepatocytesBiochemical Pharmacology, 1993
- Synthesis of biologically active taxol analogs with modified phenylisoserine side chainsJournal of Medicinal Chemistry, 1992
- New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon methodTetrahedron, 1992
- Silicon-assisted synthesis of β-lactamsTetrahedron, 1988
- Conformational control. An important factor in the stereoselective reduction of ketones by bulky hydride reagentsThe Journal of Organic Chemistry, 1977